Our one IT person also runs the phones and the copier, and they are retiring.

One person has been the network, the phones, the copier, the AV in chambers, the utility billing software liaison and the person who knows which breaker is which. They have done it well, often for a long time, and almost none of it is written down. When they retire, the town loses the documentation and the vendor relationships at the same time, because both were personal rather than institutional.

What is actually at risk:

• Credentials only they hold. Not just the admin passwords. The account at the utility billing vendor, the login for the streaming service, the alarm code, the domain registrar.
• Undocumented dependencies. The scheduled task that generates the billing file. The reason that one server cannot be rebooted during business hours. The workaround from 2019 that everything quietly depends on.
• Vendor relationships. Half the support contracts are in their name, some have lapsed, and a few vendors will only talk to them.

The best version of this, by a wide margin, is 60 to 90 days of overlap. We come in while they are still there, work alongside them, document the environment with them rather than reverse engineering it, meet the vendors, and take over function by function. It is far cheaper, it is much less disruptive, and it gives someone who has held the place together for years a proper handover instead of an abrupt one. Most of them appreciate that, and they are usually generous with what they know if the arrangement is respectful.

The worse version, which we have also done: two weeks notice, or an exit that went badly and no cooperation at all. It takes longer, it costs more, and there will be two or three surprises in the first month. It is recoverable. It is just avoidable.

Either way, what you get at the end is documentation that belongs to the town, in a form a future provider or a future employee can pick up. That is the part that should have existed all along, and it is the reason this situation is painful rather than routine.

Then you have a genuine choice: let us take it all on, or hire a replacement and have us co-manage so that one person is not carrying everything alone again. If you hire, we would gently suggest that the job description not include the copier.